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I legitimately think the phrasing on this one is wrong if you're expecting unchecking it to be the way to avoid a dark pattern. The follow-up explanation is written as though there's a double negative, but there isn't one here.
That being said, Matz also isn't a fan of static typing. Static type annotations exist in the form of RBS, but no one that matters in the Ruby eco-system is pushing static type annotations in .rb files themselves.
Also, after seeing TypeScript, I'm very happy about that.
I myself am unsure where I stand on RBS. I wouldn't mind more use of it in my gem dependencies, but would probably not like it if it was enforced everywhere.
For now I'll stick with improving my test/spec-writing skills, and maybe some runtime type checking like https://literal.fun/
I think RBS is a decent tool, I don't mind it as long as it never becomes a requirement for anything. I hate the trend of statically typed dynamic languages because it's all of the pain without the main benefit (native speed).
I set this up for my daughter on her MacBook, and she quite enjoys the custom cursors. It definitely requires some technical expertise even after installing the app though, as it doesn't ship with extra cursors; you have to configure them yourself.
Did you see his update below that paragraph? He admits that he had to update everything, and his pages are not currently a time capsule. It basically negates his entire message.
FWIW, the screenshot of the page doesn't actually look like how the page looks like currently. One could handwave and say that's intentional, but IMHO it looks as though the styles are broken (in particular the text in really small font and the yellow highlighted text)
I think the moral of the story here is that if you're going to be advocating for HTML over a SSG, then perhaps it would make sense to invest a bit of time on a styleguide page, or take a bit more effort to leverage default styles (in the style of http://motherfuckingwebsite.com/), or just commit to inline styles to lock down the individualistic look of each page (if that's what they want). Being wishy-washy about style management over time is not going to age well.
Other than that, fun project!